


I'm Hopeless Now

by anidear



Series: Keep on Truckin' [3]
Category: Batman - All Media Types, Nightwing (Comics), Red Hood and the Outlaws (Comics)
Genre: A tiny bit of angst thrown in, Alternate Universe - Modern Setting, Food Truck Owner!Jason, M/M, Mentions of parental abandonment, Mentions of parental deaths, NO CAPES, Police Officer Dick Grayson, Protective Damian Wayne, like you have to squint to see it, lots and lots of fluff, mentions of drug overdose
Language: English
Status: Completed
Published: 2020-08-20
Updated: 2020-08-20
Packaged: 2021-03-06 17:28:57
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,491
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26002684
Author URL: https://archiveofourown.org/users/anidear/pseuds/anidear
Summary: Jason takes Dick out on their first date and gives the other man a glimpse into a part of his life few know about.
Relationships: Dick Grayson & Tim Drake, Dick Grayson/Jason Todd, past Jason Todd/Rose Wilson - Relationship
Series: Keep on Truckin' [3]
Series URL: https://archiveofourown.org/series/1749466
Comments: 16
Kudos: 166





	I'm Hopeless Now

**Author's Note:**

> There is just so much fluff in here. But the next installment has some angst, not like HEAVY angst but it's there.
> 
> I'm not a Spanish speaker but there are a few Spanish phrases in this story. If there are mistakes, let me know and I'll make the edits. Google and a Cuban friend were my sources. Grammatically, I went off what I know from my Italian knowledge. But I apologize if I got anything wrong.

The dull thud of his head hitting the wall of his closet was the only sound outside of Jason’s muttering under his breath that could be heard in his place currently. He liked silence, it was steadfast, and it allowed him to think clearly. Though in the time he had spent over at Dick’s the past week, he had come to find having soft music or the tv on low volume constantly in the background was nice as well.

It had all been overpowered by Dick’s constant need to talk, but Jason hadn’t minded that either. 

Jason knew that because he had been an only child to a pair of parents that absolutely should not have been parents, he never got accustomed to constantly having people coming and going. But the time at Dick’s had showed him he could actually enjoy it. Only a small portion of the time had been just the two of them. If it wasn’t one of his brothers, then Dick’s friends (yes, he had managed to meet a couple more of the infamous harem) had an on-going rotation. Kory and Roy had proven to be Jason’s favorites so far. But from what Dick had said about Donna and Barbara, he was sure they would make that short list as well.

But while he had enjoyed the constant noise of Dick’s, right then he needed the silence he was used to because he was having a crisis: He had absolutely nothing to wear to the date he was taking Dick on in just a few hours. 

He had done his research and asked the few friends he had been able to get away from Dick to see what the other man liked, and it had all been a resounding and firm _fun_. It didn’t matter where or what, just make sure it was fun and lively because the man enjoyed life. He liked to smile, laugh, and soak in the presence of people who were enjoying themselves. Jason’s past dates had all wanted expensive and to be spoiled. Dick was the son of a billionaire and that meant he already knew expensive. And while he wasn’t spoiled, he probably knew that already as well.

With the help of Roy, he had decided on a Cuban restaurant that was one of Jason’s favorites because the music was live and the food was amazing. The staff knew him well and he loved submerging himself in the culture. It was lively and fun and there was no way someone like Dick wouldn’t love it. He was just slightly bummed that he wouldn’t be able to test out Dick’s dancing skills since he was technically still healing from being shot.

And while Jason had clothes he had worn there in the past, this was different. He was taking a date there and not just any date. Dick fucking Grayson. The first guy he had been head over heels for in a long time. The last time he had felt this strongly about someone, she had broken his heart and Jason had sworn off serious relationships. Rose had done her damage. Dick had started to heal it. Without even meaning to, he had started to mend the broken part of his heart that Jason had tried to protect and build walls around. The man was something else.

Glancing over his limited “date worthy” options, Jason gave up and grabbed a deep red sweater that had always been a crowd pleaser in the past and a pair of black slacks. Casual but polished. It would have to do. 

He grabbed the pair of shoes he usually wore with the pants he had picked out before leaving his closet and dropping the items on his bed. He had just over two hours to shower, shave, and primp before he was due at Dick’s. He could do this.

He couldn’t do this.

He wasn’t sure what he had been thinking, but standing in front of Dick’s door he was starting to second guess why a man like Dick would ever want to go on a date with a man like Jason. What could he possibly have to offer the older man? And Jason knew that this was stupid, that Dick was a smart man and wouldn’t agree to a date or even openly say he wanted to date Jason if there wasn’t something he liked about the younger man. But the panic was still there.

“There’s a security panel in his living room,” a laughing voice came from behind Jason, causing him to turn quickly to see Dick’s brother, Tim, standing there. “You know he probably knows you’ve been standing here for like five minutes freaking out, right?”

“What? I’m not…” Tim raised an eyebrow and Jason let his shoulders slump. “I’m totally freaking out and I have no idea why. What are you doing here?”

Tim held up a bag that looked like it had containers of food in it. “Alf can’t make it the normal day this week so he made the meals at the manor and asked me to drop them off. I thought you two would already be gone.”

“I’m still early.”

“I don’t care. All I want to know is if you want to come in with me now or wait to actually knock and have him open the door?”

Jason considered his options and shrugged. “Now, I guess.” Tim nodded and slipped his key into the lock, pushing the door open and heading inside. “Not like he doesn’t already know, right?” Tim laughed and headed further into the penthouse.

“Dick?! I found a dude dressed for a good time in front of your door and let him in!” Jason felt his cheeks warm at that comment but just took a deep breath and followed the path Tim took.

“What?” Dick’s muffled voice came from the direction of his bedroom before Jason watched him come out wearing a pair of dangerously low slung dark gray pants and his dark blue button up unbuttoned, exposing a tempting amount of skin. Well tempting if it hadn’t been partially marred by an angry looking healing patch of skin from his injury. “Jay! I’ll be ready in like two minutes!” Jason shrugged as he watched Dick rush over to give Tim a hug before pressing a kiss to Jason’s cheek with a whispered _you look amazing_ and rushing back into his bedroom.

“Maybe he hadn’t noticed,” Tim commented as he opened the freezer and started moving things around to fit the containers of food he had brought. “By the way, Damian ran a background check on you and is impressed at your culinary school accomplishments.” Jason sputtered at that and looked at Tim with wide eyes, but the college student wasn’t paying him any attention.

“How..? Is this a weird Wayne thing that Roy warned me about?”

“Yup.” 

“What did Roy warn you about?” Jason turned his head to look at Dick who was now completely done up and moving to the couch to pull on his socks and shoes.

“Weird Wayne things,” Tim called out, head buried in the freezer still.

“Oh yeah. Did Dames do something? Or was it Bruce this time?”

“Demon brat.”

“Don’t call him that. What did Dami do and do I need to talk to him about it?” When Tim didn’t answer, Dick glanced over at Jason to see if he knew.

“Background check. Apparently, my culinary school accomplishments are reason to be proud.” Dick looked like he was considering the actions before shrugging and going back to his shoes. “Have you done a background check on me?”

“Nah,” Dick said, standing and smoothing down his pants before moving over to where Jason was still standing and smiled up at him. “Bruce did it long before I even considered it. All I had to do was mention you one time at Family Dinner and he knew.” Knew? Dick must have seen the question in his eyes because he laughed and pressed a hand over Jason’s heart. The motion did not send a wave of warmth through his chest. Nope. “He knew I wanted to know more about you. That I would want _you_ to know more about me.”

“That predictable?” Jason teased, raising his hand to cover Dick’s.

“Maybe. Or maybe he could tell it was different this time.”

“Jeeze, now I get what Damian was complaining about. You’re disgusting.” Jason looked over to see Tim giving them a look that spoke of bad smells or unpleasant flavors. “Aren’t you guys going on a date?” Dick huffed out a laugh and Jason dropped his hand from Dick’s so the other man could move away and gather whatever else he needed. Which was a wallet from the kitchen island and a cell from the docking station near the couch. 

“All right, I’m good to go.” Dick told Jason as he double checked everything. “You’ll lock up and set alarms before you leave, Timmy?”

“I might hang out for a bit, if that’s cool? B has Selina over today and Damian is on high alert.”

“You got it. Guest room is yours if you want it.”

“But…”

Even Jason knew what that but was about and he couldn’t help but shake his head at the implication.

“What kind of harlot do you take me for, Tim? Not on the first date!” He was joking, though. With Dick? He totally would fall into his bed on the first date. If he hadn’t been shot a few weeks ago.

“Uh huh,” came the unimpressed reply. “Have fun you two. Bring back ice cream if you can.”

Dick called out his goodbye and grabbed Jason’s hand, tugging him toward the door before Jason could say much more than a goodbye as well.

“Who is Selina?” Jason asked curiously as they headed for the elevator. 

“Bruce’s on-again/off-again girlfriend. They’re obviously on at the moment.” That was all Dick offered as they stepped onto the elevator and he hit the bottom for the lobby. “So, where are we going? Roy hinted that he knew but you have been so hush hush on it.”

“That’s only because it took me a while to figure out where to take someone who has probably experienced every date worthy spot in this city.” 

Dick pressed a hand to his own chest and tried to look offended. “Are you calling me a serial dater?”

“Nah, but Wally did suggest that you had made the rounds in your circle of friends…” Jason teased, smirking.

“Hogwash,” Dick waved his hand. “I’ve never dated Kal or Donna.”

“Only those two?”

“Eh, it’s hard to keep track of who I actually dated and who I’ve just ‘had fun’ with.” Jason knew Dick was joking, thanks to Wally actually clearing up the fact that Dick had really only dated and/or slept with a small portion of their friend group and he had been joking. But the idea of Dick being so flippant about something Jason had been so serious about in his own life was a change.

“Your dating history aside, I actually just meant that I know Bruce Wayne likes to spend his money on Gothamite businesses. So, I assumed that included restaurants.”

“That’s absolutely true. But there are plenty of places I have never been.”

“And I found one, according to Roy. One that I frequent actually.” Dick raised a brow in question, the ding of the elevator reaching the lobby filling the small space. Gesturing for Dick to go first, Jason followed him toward the front door where the valet had allowed him to park his motorcycle earlier.

“I assume it’ll be good food then. A man with your talent wouldn’t accept anything less.” Jason simply nodded and thanked the man holding his keys out for him. “Are you going to tell me?” Jason just shook his head and smiled, handing Dick a helmet he had brought along before grabbing his own. Dick simply rolled his eyes and tugged the helmet on.

The ride to the restaurant was short, no more than ten minutes, but Jason was man enough to admit that he wished it were longer just for the fact that Dick would keep his arms wrapped around his waist. But since he couldn’t actually just drive randomly around the city, he settled for grabbing Dick’s hand to hold while they walked up to Havana, the music already easily heard from outside the building.

“Here?” Dick question, flicking the thumb of his free hand toward the double doors of the restaurant Jason had chosen. Jason nodded and watched Dick turn back to take in the choice. The smile that spread across his face was enough for Jason to know he had made the right choice. “I have heard about it but you’re right, I’ve never been.”

“Well, allow me to introduce you to one of the best restaurants in Gotham,” Jason told him as he tugged open one of the doors and let Dick walk in before him. The warmth of the room hit them immediately and Jason took a deep breath, letting the spices fill his senses before he smiled at Sofia, the owners daughter who happened to be the hostess for the night. “Sofia,” he greeted, smiling softly at the teenager.

“Jason, hi!” The girl smiled brightly before looking at Dick and Jason could tell the moment she recognized exactly who he was. “Oh wow.” Jason couldn’t help but chuckle, but Dick had his attention turned elsewhere so he nudged his date.

“Oh, sorry. This place is amazing,” Dick commented, looking toward Jason before turning to look at the girl who was so obviously fangirling.

“This is Sofia, she’s the owner’s daughter,” Jason supplied, and Dick turn his charming smile onto the girl. “We’ll take a table for two, Sof.” The girl nodded, but her eyes remained wide and on Dick. Not that Jason could blame her. Richard Grayson was a beloved celebrity of Gotham. Bruce had his own following, but Dick was considered the sweetheart of the city. He charmed everyone who came into contact with him.

“This way,” the girl said, trying to maintain some sort of professional appeal as she led them to Jason’s favorite spot and set their menus down before they took their seats. “Jorge will be over in a minute. Do you want the usual drink?” Being a regular meant the staff knew Jason’s favorites but they didn’t know Dick’s.

“I’ll wait for Jorge,” he told her, and she nodded with a smile, glancing one last time to Dick who flashed her another bright smile, before she rushed off. “You have a fan.”

Dick snorted and picked up the menu. “I tend to have them everywhere. She was sweet though.” And Jason just couldn’t get over that. How could someone be so used to that sort of attention? “So tell me, Mr. Todd, what is your usual?”

“They make a fantastic daiquiri,” Jason shrugged, unapologetic from the seemingly “feminine” cocktail.

“That we do!” Jason looked over to find the familiar waiter standing by their table, smiling at the two of them. Though, Jason could see the question in his eye when his gaze landed on Dick and moved back to Jason. “Shall I have two whipped up? It’s mango season and we just had a fresh batch delivered.”

“Oh yes, that sound like heaven.” Dick’s reply surprised him, but it probably shouldn’t have. So, he simply nodded his agreement.

“And the usual chips and dip, mi amigo?” Jason nodded and Jorge headed off to the bar to take care of the starters.

“You know, I should be upset you brought me to a place made for dancing when I’m under strict orders to avoid it,” Dick drew his attention. Jason leaned his elbows on the table and smiled at Dick, shrugging a shoulder.

“When you’re given the all clear, I’m more than happy to bring you back just to get you on that dance floor.”

“I’ll be holding you to that,” Dick smiled, leaning onto the table as well. And there was no doubt in Jason’s mind that he would do just that. “So you come here enough that you have regular orders and the waiter calls you his friend.”

Jason shrugged a shoulder. “Jorge calls everyone friend.” Dick raised an eyebrow and Jason couldn’t help but chuckle. “Okay fine, yes. I come here at least once a week. Most of the time I carry out, but a couple times a month I eat in. A lot of them also order from my truck.”

And Jason had really liked that they respected him as a customer enough to try and support him as well. It was a true brotherhood of sorts. And a lot of Gotham had that same vibe. You look after me, so I look after you.

Jason kept his eyes on Dick and observed him taking in everything around them. It was so strange to see someone who wanted to take it all in. In the past, his dates had always been more focused on the moment between them. But this sort of air between them spoke of comfort and not feeling like they had to impress each other. They had already done that. Jason was already gone and he could tell in the small touches and the smiles that Dick was right there with him. 

So instead of focusing on Jason, Dick’s eyes scanned the room. Jason watched his head bob to the upbeat music coming from the stage. He saw the longing as sapphire eyes drifted over the couples dancing, pausing at a mother/son pair that caused what looked like pain to spill into his eyes. But it was gone as quickly as Dick moved his eyes over to the bar area where there were rowdy customers enjoying a sporting event while drinking.

“This place is magical,” Dick said, finally turning his eyes back to Jason. The smile on his face was comfortable and relaxed. He looked no different than when they were on the couch eating a meal Jason had prepared. And Jason couldn’t help but feel the same. 

The moment was broken by the return of Jorge with their drinks and the chips. He gave a warning to Dick about the spice levels of the salsas he had put down but Dick simply waved a hand at that and went right for the hottest. And since Jason had already made his spicy chili for the man and had watched him not bat an eyelash, he just watched Jorge’s eyes widen as Dick showed no signs of trauma as he went in for another.

“Ay amigo encontraste uno bueno,” Jorge clapped Jason on the shoulder with a bright laugh and Dick smirked. Jorge probably had no idea Dick could understand. “Do you know what you’d like?”

Jason looked over at Dick and raised an eyebrow to see if he knew what he would like. Dick held up a finger and opened the menu quickly to scan it as he chewed before swallowing. “Oh, you do have it! Rabo encendido, por favor,” Dick said, accent perfectly on point and Jason tried not to take too much pleasure out of Jorge’s surprise.

“Si, best there is amigo.” Jorge looked over at Jason who simply nodded as he grabbed Dick’s menu and handed both his and Dick’s over to Jorge. “Alejandra is in the back, I’ll let her know you’re here. She’ll want to meet _tu cita_.” Dick’s laughter as Jorge walked away was worth the flush he could feel on his face at the teasing.

“Hey,” Dick pulled his attention away from him watching Jorge head to the kitchen. He found Dick with his drink raised for a cheers and a cheeky smile on his face. “To us? It only took us forever to get to this point, but I’m glad we’re here.”

Jason grabbed his glass and clinked it with Dick’s, his smile going soft and that warm feeling in his chest returning. “Yeah, to you not dying and me not thinking you just ditched me.” Dick snorted into his cup and Jason wanted to pinch himself because how could that action be just as endearing as the moment they had earlier with Dick’s hand pressed over his heart and his own hand covering Dick’s? He was a goner. There was no hope for him in that moment. None at all.

The ease the date started with continued on through the meals and Jason found himself enjoying a more lively side of Dick as he fed off the environment of the room. The cheerful banter he exchanged with the owner of the restaurant and Jorge left Jason even more glad he had decided on a place that meant something to him personally. Yes, there were other restaurants in the city that he was considered a regular at, but not like this. Not since Alejandra had known the woman who had raised him. How he had stayed at the Rivera house after she had died. But Dick didn’t know any of that. He didn’t know how much this place meant to him and the impact it had on his career choice because Jason had never told him. Instead he watched Dick form his own opinion on the people he cared about and let him charm them without any influence.

“You know,” Dick’s voice pulled him out of his thoughts, drawing ocean blue eyes to sapphire. “You haven’t told me how you came to be a regular here.” His eyes were bright, cheeks splashed with red from the alcohol consumption, and his smile loose. A smile always so freely given.

“I’ve known Alejandra since I was young. She helped me when I had no one else.” He watched Dick tilt his head to the side, prompting him to continue. Taking a deep breath, Jason let it out slowly and steeled himself for sharing this. “She was my mother’s friend, the only one that I know of outside of her drug addicted friends.” Swirling the melted frozen drink in his glass, he let his eyes slip just past Dick’s shoulder. “When my dad just stopped coming home, I spent a lot of time with Alejandra because my mother wasn’t exactly a good parent. And when Catherine died of an OD, Alejandra took me in.”

The hand that appeared over the one still swirling his drink around caught Jason off guard and he looked back to Dick. “You don’t have to do this here. I didn’t know, I’m sorry.” And it struck him again, with those words, that he really had no idea how he had managed to score a guy like Dick. His date who just wanted to know more about the past that Jason kept under lock and key. 

“I want to tell you.” Which was absolutely the truth. Jason wanted to let Dick into every corner of his life, let him fill in the empty spaces of his heart. “But maybe not here.” He watched Dick nod in understanding and Jason felt his shoulders relax a little. He hadn’t even noticed that he had tensed up, but obviously Dick had.

“Let’s square up here and then head back toward my place. There’s a gelato place a block away that Timmy likes the best, we can take a walk. Looks like a nice night.”

Jason sighed and smiled. “Yeah, that sounds perfect.” With a glance over his shoulder, Jason coughed Jorge’s attention and the man gave a nod before getting to work on closing their tab. Jason pushed to his feet and looked at Dick who’s brow had furrowed in an adorably confused expression. “They have my card on file. And Jorge knows to add 25% each time.”

“I was thinking we could split the bill, though…” Jason laughed at that idea. The glare Dick sent him was just as cute as the confusion and Jason just held out his hand to help Dick out of his own chair. “Fine, but I get to pay for the gelato.”

“Sure thing, Handsome. Sure thing.” 

Dick gracefully got to his feet and brushed off phantom crumbs while keeping hold of Jason’s hand. Jason watched him in amusement before letting the older man lead him toward the exit.

“Bye Jay! Bye Dick,” Sofia called out from her post near the door. Jason paused to kiss the girl’s cheek and Dick gave her his blinding smile and a wave before the pair slipped back out into the cooling Gotham night air.

The pair were silent as they made their way back to Jason’s motorcycle and then back to Dick’s apartment building. It wasn’t until they were close to the gelato shop that Dick paused and turned to face Jason.

“Before we’re back in a crowd of people or with Timmy, I just wanted to say thank you. Not just for the amazing night, but for letting me into that piece of your life. I don’t ask about your past because I can tell it’s private. And if you want to tell me one day, then I’ll be happy to listen,” he spoke softly and Jason just remained silent, letting him say his piece. “But don’t think you ever have to tell me anything you don’t want to talk about. There are things that will take me a while to talk about and I know you’ll respect that. I just want to make sure you know that I’ll do the same.”

Waiting a moment to be sure that Dick was done, Jason took a step closer and placed the hand not still being held by Dick’s onto the older man’s cheek. “I don’t know what I did to deserve someone like you, but I’m really fucking glad I did it.” He cut Dick’s responding laugh off with his mouth, pressing their lips together in a way not too dissimilar to the kiss they had shared in the hospital not too long ago.

The feeling of Dick’s hand slipping around his hip to clench at his sweater on back told him that he had made the right move. The press of their bodies together coupled with the hum of approval from Dick was all the encouragement Jason needed to slip his hand from Dick’s cheek to his hair to angle the other man’s head just so.

When Jason finally pulled back, he couldn’t help but smile at the sight of Dick chasing his lips. “Let’s get that ice cream and head back to give your brother some.”

“If you’re interested, we can put in a movie?” It was the first time Dick had sounded a bit hesitant with him since they had decided to give a relationship a try and it made Jason’s heart clench a little.

“That sounds perfect.” Dick’s responding smile had Jason leaning forward for one more kiss before they walked the rest of the way to the gelato shop.

**Author's Note:**

> Feel free to hit me up on Tumblr [here](https://tumblr.com/composetheheart)
> 
> Translations:  
> mi amigo: my friend  
> Ay amigo encontraste uno bueno: Oh friend, you found a good one  
> tu cita: your date


End file.
